Synthesis of new disulfonamides from different substituted diamino pyridines

Behmadi, Hossein; Saadati, Seyed Mahdi; Roshani, Mina; Ghaemy, Mousa

doi:10.1590/s0100-46702009000300003

Cited by 6 publications

(2 citation statements)

References 22 publications

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“…Sulfonamides constitute a useful group of compounds with extensive applications in medicinal and synthetic chemistry [ 1 , 2 , 3 , 4 ], with the sulfonamide functional group being a major building block for many therapeutic molecules [ 3 , 4 ] and natural products. Consequently, these applications have paved the way for the continuous search and design of new drug formulations based on this class of compounds.…”

Section: Introductionmentioning

confidence: 99%

Structure and Computational Studies of New Sulfonamide Compound: {(4-nitrophenyl)sulfonyl}tryptophan

et al. 2022

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Synthesis of sulfonamide through an indirect method that avoids contamination of the product with no need for purification has been carried out using the indirect process. Here, we report the synthesis of a novel sulfonamide compound, ({4-nitrophenyl}sulfonyl)tryptophan (DNSPA) from 4-nitrobenzenesulphonylchloride and L-tryptophan precursors. The slow evaporation method was used to form single crystals of the named compound from methanolic solution. The compound was characterized by X-ray crystallographic analysis and spectroscopic methods (NMR, IR, mass spectrometry, and UV-vis). The sulfonamide N-H NMR signal at 8.07–8.09 ppm and S-N stretching vibration at 931 cm−1 indicate the formation of the target compound. The compound crystallized in the monoclinic crystal system and P21 space group with four molecules of the compound in the asymmetric unit. Molecular aggregation in the crystal structure revealed a 12-molecule aggregate synthon sustained by O-H⋯O hydrogen bonds and stabilised by N-H⋯O intermolecular contacts. Experimental studies were complemented by DFT calculations at the B3LYP/6-311++G(d,p) level of theory. The computed structural and spectroscopic data are in good agreement with those obtained experimentally. The energies of interactions between the units making up the molecule were calculated. Molecular docking studies showed that DNSPA has a binding energy of −6.37 kcal/mol for E. coli DNA gyrase (5MMN) and −6.35 kcal/mol for COVID-19 main protease (6LU7).

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Section: Introductionmentioning

confidence: 99%

Structure and Computational Studies of New Sulfonamide Compound: {(4-nitrophenyl)sulfonyl}tryptophan

et al. 2022

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“…Among the broad range of compounds tested as potential anticancer agents, derivatives of sulfamide have attracted reasonable attention [15]. Sulfonamide derivatives include an important class of drugs with different biological activities [16], and many of them are widely used in therapy as antihypertensive, antibacterial, anti-inflammatory, anti-thyroid [17] [18], and hypoglycemic [19], diuretic and receptor tyrosine kinase inhibitors [1]. Recently, a host of structurally novel sulfonamide derivatives have been reported to show anticancer activity in vivo and/or in vitro [20] [21].…”

Section: Introductionmentioning

confidence: 99%